Question
3) what is the molecule according to the following spectroscopic information?
4) propose a synthetic route for the answer in question 3 starting with benzene.

3. What is the molecule according to the following spectroscopic information? Parts list and product VAN IR Spectrum 2000 150
4. Propose a synthetic route for the answer to the problem in question three starting with benzene,
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Answer #1

The molecule could be

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Molecular formula : C7H6Cl2

Double bond equivalent calculation

C + 1 - H/2 - X/2 = 4

Presence of a benzene group

PPM

733 7.33 729

There are two different types of hydrgen, thus the benzene is monosubstituted

the substituent on benzene would be -CHCl2

Mass spectrum confirms the existence of 2 chlorines on the same carbon

Mass Spectrum Ven 18012004 he 180 120 160 200 20 260 /

C- 13 NMR also suggests there are 5 different carbons

140 120 100 80 PPM 60 40

CI 772/CI 125.9 125.9 128.8 128.8 129.9

C-H str C=C str IR Spectrum C-Cl str 4000 1200 2000 V BOO com

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